Imidazole, 5-(2-chloroethyl)-1-methyl-2-nitro- → 1-ME-2-NO2-5-Vinyl imidazole

HRID 1075962Notes

Reaction equation

HRID 1075962 reaction equation
Cl[CH2:2][CH2:3][C:4]1[N:8]([CH3:9])[C:7]([N+:10]([O-:12])=[O:11])=[N:6][CH:5]=1.CC(C)([O-])C.[K+]>C1C=CC=CC=1>[CH3:9][N:8]1[C:4]([CH:3]=[CH2:2])=[CH:5][N:6]=[C:7]1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 90183Imidazole, 5-(2-chloroethyl)-1-methyl-2-nitro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 932151-ME-2-NO2-5-Vinyl imidazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 18.9 g. of 5-(2-chloroethyl)-1-methyl-2-nitroimidazole (prepared according to the procedure of British Pat. No. 1,222,486) in 2.8 liters of anhydrous benzene cooled to 5°-10° C., 16.8 g. of potassium tert-butoxide is added. Stirring is continued for 2 hours at 5°-10° C. After filtration and concentration to dryness under vacuum at a temperature lower than 50° C., the resulting yellow oily residue is washed three times with 50 ml. of ethyl ether (or light petroleum). The title product is obtained, which is dried under vacuum at 40° C.; yield 12 g. (77.7%). A sample crystallized from ethyl ether melts at 106°-108° C.

Workup

  1. filtrationAfter filtration and concentration to dryness under vacuum at a temperature lower than 50° C.
  2. washthe resulting yellow oily residue is washed three times with 50 ml

Sources & evidence

ORD record
ord-1dc4c2dcbd484499bf4d0d95e7d51419
Source dataset
uspto-grants-1976_05
Patent number
US03954789

Reaction notes

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